5-(4-hydroxymethylphenyl)-10,15,20-tris(4-methylphenyl)porphyrin | 121869-50-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四吡咯及其衍生物
• 英文名称: 5-(4-hydroxymethylphenyl)-10,15,20-tris(4-methylphenyl)porphyrin
• 英文别名: 5-[4-(hydroxymethyl)phenyl]-10,15,20-tri-p-tolylporphyrin；5-(4'-hydroxymethylphenyl)-10,15,20-tritolylporphine；5-(p-Hydroxymethylphenyl)-10,15,20-tri(p-methylphenyl)porphine；5-(4-hydroxymethylphenyl)-10,15,20-tri-p-tolylporphyrin；5-(4-(hydroxymethyl)phenyl)-10,15,20-tritolylporphyrin
• CAS: 121869-50-9
• 化学式: C₄₈H₃₈N₄O
• 分子量: 686.856
• InChiKey: QODRVKYPMHUTPN-PJEPRTEXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.74
• 重原子数：
  53.0
• 可旋转键数：
  5.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  77.59
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  5-(4-hydroxymethylphenyl)-10,15,20-tris(4-methylphenyl)porphyrin 在 thallium (III) chloride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 48.0h， 以78%的产率得到chloro[5-[4-(hydroxymethyl)phenyl]-10,15,20-tri-p-tolylporphinato]thallium(III)
  参考文献：
  名称：

  Synthesis of oligo(p-phenylene)-linked dyads containing free base, zinc(II) or thallium(III) porphyrins for studies in artificial photosynthesis

  摘要：

  A series of (p-phenylene)(n)-linked meso-mesityl-substituted porphyrin dyads (n=2-4) was prepared via Suzuki coupling of zinc(II) and free base porphyrin building blocks. The resulting zinc(II)/free base porphyrin dyads were demetalated. The series of free base porphyrin dimers (n=1-4), four other porphyrin dimers (with p-phenylene, diphenylethyne or diphenylbutadiyne linkers; and aryl or tridec-7-yl meso substituents), and several benchmark monomers were converted to the thallium(III)chloride complexes under mild conditions. The collection of eight Tl(III)Cl/Tl(III)Cl dimers is designed for studies of ground-state hole-transfer processes and comparison with the excited-state energy- and hole-transfer processes of the corresponding Zn(II)/free base dyads. Altogether, 18 new porphyrin arrays and benchmark monomers have been prepared. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.05.059
• 作为产物：
  描述：

  Zn(II)-5-[4-(hydroxymethyl)phenyl]-10,15,20-tri-ptolylporphyrin 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以254 mg的产率得到5-(4-hydroxymethylphenyl)-10,15,20-tris(4-methylphenyl)porphyrin
  参考文献：
  名称：

  B,B-Diporphyrinbenzyloxy-BODIPY Dyes: Synthesis and Antenna Effect

  摘要：

  B,B-Diporphyrinbenzyloxy-BODIPY derivatives have been prepared in high yields, and the photophysical properties are reported. Singlet energy transfers from BODIPY to the porphyrin units have been analyzed.

  DOI：

  10.1021/jo3000833

文献信息

• Nearly Chromatography-Free Synthesis of the A₃B-Porphyrin 5-(4-Hydroxymethylphenyl)-10,15,20-tri-<i>p</i>-tolylporphinatozinc(II)
  作者：Syeda Huma H. Zaidi、Robert S. Loewe、Brad A. Clark、Marc J. Jacob、Jonathan S. Lindsey

  DOI：10.1021/op0502553

  日期：2006.3.1

  to give the dipyrromethane (versus 100 equiv previously), (ii) 1,9-diacylation of a dipyrromethane using the hindered Grignard reagent 2,6-dimethylphenylmagnesium bromide and p-toluoyl chloride to give the 1,9-diacyl versus 1-acyl products in >10:1 ratio (versus 4:1 using EtMgBr), (iii) isolation of the dibutyltin complex of the 1,9-diacyldipyrromethane from the crude reaction mixture by direct crystallization

  合成卟啉具有不同介孔取代基的合理途径通常已在中等规模（<1 g量）下实施。在A 3 B-卟啉5-（4-羟甲基苯基）-10,15,20-三- p -tolylporphinatozinc（II）（Zn的1）是必需的多克量的在信息存储应用可能的商业用途。Zn-1的合成是通过5-（4-羟甲基苯基）二吡咯甲烷与1,9-二-对-甲苯基-5- p衍生的二甲醇反应而进行的-甲苯基吡咯甲烷。对导致二吡咯甲烷和二吡咯甲烷-二甲醇的步骤进行了四项改进：（i）在醛的缩合反应中使用50当量的吡咯得到二吡咯甲烷（之前为100当量），（ii）1,9-使用受阻的格氏试剂2,6-二甲基苯基溴化镁和对甲苯甲酰氯对二吡咯甲烷进行二酰化反应，从而以> 10：1的比例得到1,9-二酰基对1-酰基的产物（使用EtMgBr则为4：1），（iii ）通过使用甲醇/甲基叔丁基酯直接结晶从粗反应混合物中分离出1,9-二酰基二吡咯甲烷的二丁
• An efficient synthesis of tetraaryl porphyrins substituted with ester groups bearing long alkyl chains
  作者：Hermann K. Hombrecher、Stefan Ohm

  DOI：10.1016/s0040-4020(01)86323-7

  日期：1993.3

  The synthesis of tetraaryl porphyrins substituted with long chain ester groups is described. The compounds are conveniently prepared from the methyl ester 1a via a based induced transesterification procedure. The method is also applicable for the synthesis of ester linked diporphyrins.

  描述了被长链酯基取代的四芳基卟啉的合成。该化合物可通过基于基础的酯交换步骤，方便地由甲酯1a制备。该方法也适用于酯连接的双卟啉的合成。
• Cooperative porphyrin-quadrupolar based triad for combined two-photon induced fluorescence and singlet oxygen generation
  作者：Jean-Baptiste Verlhac、Guillaume Clermont、Mireille Blanchard-Desce

  DOI：10.1142/s1088424616501248

  日期：2017.2

  design. As a result, the two-photon absorption induced singlet oxygen generation efficiency of the triad in the NIR region is found to be enhanced by an order of magnitude as compared to the porphyin subunit. Potential applications of these porphyrin-based multichromophoric systems for photodynamic therapy based upon two-photon excitation in the NIR region might be possible since it overcomes the low two-photon

  结合芴核双供体四极染料的大双光子吸收特性和卟啉亚基的显着敏化特性（即高系统间交叉和通过能量产生单线态氧的能力）的协同多发色三联体系统的设计和合成描述了从其三重激发态向氧的转移）。辐照后，能量可以通过 FRET 过程以 80% 的效率从四极发色团转移到卟啉。此外，四极亚基的双光子吸收特性和卟啉的敏化和荧光特性都得到了保留，这表明由于实施的设计，在这种分子结构中可以防止有害的竞争过程（例如光诱导电子转移）。结果发现，与卟啉亚基相比，近红外区域三联体的双光子吸收诱导单线态氧生成效率提高了一个数量级。这些基于卟啉的多发色系统在近红外区域基于双光子激发的光动力治疗中的潜在应用可能是可能的，因为它克服了卟啉的低双光子吸收响应，同时完全保留了它们显着的光敏特性。发现与卟啉亚基相比，近红外区域三联体的双光子吸收诱导的单线态氧生成效率提高了一个数量级。这些基于卟啉的多发色系统在近红外区域基于双光子激发的光动
• Ono, Noboru; Tomita, Hiroaki; Maruyama, Kazuhiro, Journal of the Chemical Society. Perkin transactions I, 1992, # 19, p. 2453 - 2456
  作者：Ono, Noboru、Tomita, Hiroaki、Maruyama, Kazuhiro

  DOI：——

  日期：——
• Molecular tweezer based on zinc porphyrin-substituted diarylethene
  作者：Ji Eun Park、Eun Ju Shin

  DOI：10.1016/j.saa.2006.12.027

  日期：2007.11

  A molecular tweezer, zinc porphyrin-dithienylethene-zinc porphyrin (ZnP-DTE-ZnP) triad, has been prepared. Triad ZnPor-DTE-ZnPor showed a little electronic communication among the chromophores judged from the comparison of the steady-state absorption and fluorescence spectra for triads and their component compounds. Irradiation of ZnPor-DTE-ZnPor with UV light converts dithienylethene moiety from open form to closed form. The complexation of ZnP-DTE-ZnP with 4,4'-bipyridyl were investigated by absorption and fluorescence spectroscopic measurements. ZnP-DTE-ZnP forms a 1:1 complex with 4,4'-bipyridyl. The stability constants of log K = 4.0 and 4.2 mol(-1) dm(3) were determined by absorption and fluorescence spectral changes, respectively. (C) 2006 Elsevier B.V. All rights reserved.